research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026009497

Structure of metaraminol hydrogen tartrate from synchrotron X-ray data and density functional theory calculations

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Jacob K. Salazar,a James A Kaduk,b* Anja Dosenc and Thomas N. Blantonc

aNorth Central College, Department of Chemistry, 131 S. Loomis St., Naperville IL 60540, USA, bNorth Central College, Department of Physics, 131 S Loomis St, Naperville IL 60540, USA, and cICDD, 12 Campus Blvd., Newtown Square PA 19073-3273, USA
*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 28 July 2026; accepted 10 September 2026; online 15 September 2026)

The crystal structure of the title salt, C9H14NO2+·HC4H4O6−, has been solved and refined using synchrotron X-ray powder diffraction data and optimized using density functional theory techniques. The crystal structure consists of alternating hydro­phobic and hydro­philic layers lying parallel to the ab plane. Hydrogen bonds link the cations and anions in the hydro­philic layers. The anions are linked by very strong charge-assisted O—H⋯O hydrogen bonds into chains propagating along the a-axis direction. Each H atom of the protonated N atom of the cation acts as a donor in at least one N—H⋯O hydrogen bond to an anion.

CCDC references: 2587069; 2587068

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1. Chemical context

Metaraminol hydrogen tartrate, C9H14NO2+·HC4H4O6− (I), also known as metaraminol bitartrate, and marketed as Aramine (obsolete), Pressonex and others in various countries, is used to treat hypotension (low blood pressure), particularly associated with patients receiving spinal anesthesia (Grauslyte et al., 2022View full citation). The systematic name (CAS Registry Number 33402-03-8) is 3-[(1R,2S)-2-azaniumyl-1-hy­droxy­prop­yl]phenol (2S,3S)-hydrogen 2,3-di­hydroxy­but­ane­dioate.

[Scheme 1]

This work was carried out as part of a project (Kaduk et al., 2014View full citation) to determine the crystal structures of large-volume commercial pharmaceuticals, and includes high-quality powder diffraction data for them in the Powder Diffraction File (Kabekkodu et al., 2024View full citation).

2. Structural commentary

The asymmetric unit of (I) is illustrated in Fig. 1[link] and consists of one C9H14NO2+ cation and one HC4H4O6− anion in space group P212121. The root-mean-square difference of the non-H atoms in the Rietveld-refined and VASP-optimized structures of (I), calculated using the Mercury (Macrae et al., 2020View full citation) CSD-Materials/search/crystal packing similarity tool is 0.325 Å. The root-mean-square Cartesian displacements of the non-H atoms in the refined and optimized structures of the cation and anion, calculated using the Mercury calculate/mol­ecule overlay tool, are 0.235 and 0.167 Å, respectively (Figs. 2[link] and 3[link]). The agreements are within the normal range for correct structures (van de Streek & Neumann, 2014View full citation). The remaining discussion will emphasize the VASP-optimized structure.

[Figure 1]
Figure 1
The asymmetric unit of (I), with the atom numbering. The atoms are represented by 50% probability spheroids.
[Figure 2]
Figure 2
Comparison of the refined structure of the metaraminol cation in (I) (red) to the VASP-optimized structure (blue). The comparison was generated using the Mercury calculate/mol­ecule overlay tool; the r.m.s. difference is 0.235 Å.
[Figure 3]
Figure 3
Comparison of the refined structure of the bitartrate anion in (I) (red) to the VASP-optimized structure (blue). The comparison was generated using the Mercury calculate/mol­ecule overlay tool; the r.m.s. difference is 0.167 Å.

Almost all of the bond distances, bond angles, and torsion angles fall within the normal ranges indicated by a Mercury Mogul geometry check (Macrae et al., 2020View full citation). Only the C7—C5—C4 bond angle of 117.1° [average = 114.1 (9)°; Z-score = 3.4] is flagged as unusual. The standard uncertainty on the average is very small, inflating the Z-score, so this angle is not of concern. The conformation about the C6—C4—C5—N3 torsion angle is trans (179.2°), and falls within the normal distribution. The torsion angles involving rotation about the C4—C6 bond (such as 77.9° for C5—C4—C6—C8) fall within the typical broad ranges for similar torsion angles. The tartrate anion is in the trans conformation, as indicated by the C35—C34—C32—C33 torsion angle of −177.2°.

Quantum chemical geometry optimizations of the isolated metaraminol cation and bitartrate anion (DFT/B3LYP/6-31G*/water) using Spartan '24 (Wavefunction, 2025View full citation) indicated that both the cation and anion were geometrically (r.m.s. difference = 0.277 and 0.173 Å, respectively) similar to local minima, but energetically different (6.1 and 21.2 kcal mol−1, respectively). The global minimum-energy conformations were found to be more compact (featuring intra­molecular hydrogen bonds), showing that inter­molecular inter­actions are important in determining the solid-state conformations of these species in (I).

3. Supra­molecular features

The extended structure of (I) (Fig. 4[link]) consists of alternating hydro­phobic and hydro­philic layers lying parallel to the ab plane. Hydrogen bonds (discussed below) link the cations and anions in the hydro­philic layers. The Mercury aromatics analyser indicated one strong (d = 4.97 Å) inter­action between the phenyl rings of the cations, and two moderate (d = 6.15 Å) inter­actions. The mean plane of the phenyl ring in the asymmetric unit is approximately (Mathematical equation11).

[Figure 4]
Figure 4
The crystal structure of (I), viewed down the b-axis direction.

Analysis of the contributions to the total crystal energy of the structure using the Forcite module of Materials Studio (Dassault Systèmes, 2025View full citation) indicated that bond, angle, and torsion distortion terms contribute significantly to the intra­molecular energy. The inter­molecular energy is small, and is dominated by van der Waals attractions, which in this force field-based analysis includes hydrogen bonds. The hydrogen bonds are better discussed using the results of the DFT calculation.

Hydrogen bonds (Table 1[link]) are prominent in the structure. The anions are linked by very strong charge-assisted O29—H41⋯O26 hydrogen bonds into chains propagating along the a-axis direction. The O29—H41 single bond has a Mulliken overlap population of 0.175 e, with a bond energy [calculated using the correlation of Rammohan & Kaduk (2018View full citation)] of 23.9 kcal mol−1. The H41⋯O26 hydrogen bond is only slightly weaker, with an overlap population of 0.117 e and a bond energy of 18.7 kcal mol−1. Both alcoholic hydroxyl groups of the hydrogen tartrate anion act as donors in O—H⋯O hydrogen bonds, one to another anion and one to a cation.

Table 1
Hydrogen-bond geometry (Å, °)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O29—H41⋯O26i 1.14 1.33 2.464 173
O30—H37⋯O1 0.99 1.70 2.686 169
O31—H36⋯O29ii 0.99 1.95 2.885 156
O31—H36⋯O28 0.99 2.36 2.644 96
N3—H40⋯O31iii 1.05 1.72 2.762 172
N3—H21⋯O28ii 1.05 1.69 2.718 166
N3—H20⋯O27 1.05 1.78 2.796 161
N3—H20⋯O30 1.05 2.50 3.111 116
O2—H25⋯O27iv 1.00 1.76 2.709 157
O1—H22⋯O2iv 0.98 2.19 3.113 155
C5—H14⋯O26 1.10 2.40 3.364 145
C12—H24⋯O26 1.09 2.72 3.758 154
C4—H13⋯O28 1.11 2.61 3.410 128
C9—H19⋯O29 1.09 2.95 4.033 171
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation; (iv) Mathematical equation.

Each H atom of the protonated –N3H3+ grouping of the cation acts as a donor in at least one N—H⋯O hydrogen bond to an anion. The energies of these hydrogen bonds were calculated using the correlation of Wheatley & Kaduk (2019View full citation). One hydroxyl group of the cation forms an O—H⋯O hydrogen bond to another cation, while the other bonds to the anion. Several C—H⋯O hydrogen bonds (from both the cation and anion) also contribute to the cohesion of the structure.

The volume enclosed by the Hirshfeld surface of (I) (Fig. 5[link]; Spackman et al., 2021View full citation) is 366.73 Å3, or 98.13% of 1/4 of the unit-cell volume. The packing density is thus typical. The close contacts (red in Fig. 5[link]) correspond to the hydrogen bonds noted above. The volume per non-hydrogen atom is slightly smaller than normal, at 17.0 Å3.

[Figure 5]
Figure 5
The Hirshfeld surface of (I). Inter­molecular contacts longer than the sums of the van der Waals radii are colored blue, and contacts shorter than the sums of the radii are colored red. Contacts equal to the sums of radii are white.

The Bravais–Friedel–Donnay–Harker (Bravais, 1866View full citation; Friedel, 1907View full citation; Donnay & Harker, 1937View full citation) algorithm suggests that we might expect platy morphology for (I), with {001} as the principal faces. A second-order spherical harmonic model for preferred orientation was included. The texture index was 1.001, indicating that the preferred orientation was negligible in this rotated capillary specimen.

4. Database survey

A process for preparing metaraminol bitartrate is claimed in US Patent 10,087,136 B2 (Brenna et al., 2018View full citation; Laboratori Alchemia S.r.l.), which includes NMR data, but no X-ray diffraction data, is provided. A synthesis method for metaraminol bitartrate is also claimed in Chinese Patent CN 103739504A (Pu et al., 2013View full citation; Guangzhou Person Pharmaceutical Co., Ltd.). We are unaware of any published diffraction data for metaraminol bitartrate.

A reduced cell search in the Cambridge Structural Database (CSD version 2026.1.0; Groom et al., 2016View full citation), combined with the chemistry C, H, N, and O only, yielded 31 hits, but no structures of metaraminol or its derivatives.

5. Synthesis and crystallization

Metaraminolhydrogen tartrate is a commercial reagent, purchased from TargetMol (Batch #118859), and was used as received.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The white powder was packed into a 1.5 mm diameter Kapton capillary, and rotated during the measurement at ∼50 Hz. The powder pattern was measured at 295 K at beam line 11-BM (Lee et al., 2008View full citation; Wang et al., 2008View full citation; Antao et al., 2008View full citation) of the Advanced Photon Source at Argonne National Laboratory using a wavelength of 0.4687342 Å from 0.5–50° 2θ with a step size of 0.001° and a counting time of 0.1 sec step−1. The high-resolution powder diffraction data were collected using twelve silicon crystal analyzers that allow for high angular resolution, high precision, and accurate peak positions. A mixture of silicon (NIST SRM 640c) and alumina (NIST SRM 676a) standards (ratio Al2O3:Si = 2:1 by weight) was used to calibrate the instrument and refine the monochromatic wavelength used in the experiment.

Table 2
Experimental details

  (I)
Crystal data
Chemical formula C9H14NO2+·C4H5O6−
Mr 317.29
Crystal system, space group Orthorhombic, P212121
Temperature (K) 295
a, b, c (Å) 7.190512 (12), 8.421634 (17), 24.69323 (5)
V (Å3) 1495.32 (1)
Z 4
Radiation type Synchrotron, λ = 0.46873 Å
μ (mm−1) 0.001
Specimen shape, size (mm) Cylinder, 2.0 × 1.5
 
Data collection
Diffractometer 11-BM, APS
Specimen mounting Kapton capillary
Data collection mode Transmission
Scan method Step
2θ values (°) 2θmin = 0.510, 2θmax = 49.995, 2θstep = 0.001
 
Refinement
R factors and goodness of fit Rp = 0.090, Rwp = 0.105, Rexp = 0.039, R(F2) = 0.09024, χ2 = 7.530
No. of parameters 85
No. of restraints 50
(Δ/σ)max 2.873
Computer programs: GSAS-II (Toby & Von Dreele, 2013View full citation) and DIAMOND (Crystal Impact, 2025View full citation).

The pattern was indexed on a primitive ortho­rhom­bic unit cell with a = 7.19584, b = 8.42890, c = 24.73316 Å, V = 1500.14 Å3, and Z = 4 using JADE Pro (MDI, 2025View full citation). The suggested space group was P212121, which was confirmed by the successful solution and refinement of the structure.

The mol­ecular structure of metaraminol was downloaded from PubChem (Kim et al., 2023View full citation) as Conformer3D_COMPOUND_CID_5906.sdf. It was converted to a *.mol2 file using Mercury (Macrae et al., 2020View full citation), and to a Fenske–Hall Z-matrix using Open Babel (O'Boyle et al., 2011View full citation). The tartrate anion model was taken from our structure of eliglustat hemitartrate (Kaduk et al., 2026View full citation). The structure was solved using Monte Carlo simulated annealing techniques as implemented in DASH (David et al., 2006View full citation), EXPO2014 (Altomare et al., 2013View full citation), and FOX (Favre-Nicolin & Černý, 2002View full citation). All three programs yielded essentially the same structure. The EXPO2014 model was chosen for refinement.

Atom H40 was added to protonate N3 using Materials Studio (Dassault Systèmes, 2025View full citation). Analysis of O⋯O distances for potential hydrogen bonds suggested that O29 was protonated (O29⋯O26 = 2.39 Å), so H41 was added 0.90 Å from O29 on the O29⋯O26 vector using Materials Studio.

Rietveld refinement was carried out using GSAS-II (Toby & Von Dreele, 2013View full citation). Only the 1.5–28.0° portion of the pattern was included in the refinement (dmin = 0.969 Å). All non-H bond distances and angles were subjected to restraints, based on a Mercury/Mogul Geometry Check (Sykes et al., 2011View full citation; Bruno et al., 2004View full citation). The Mogul average and standard deviation for each qu­antity were used as the restraint parameters. The phenyl ring was restrained to be planar. The restraints contributed 1.5% to the overall χ2. The hydrogen atoms were included in calculated positions, which were recalculated during the refinement using Materials Studio (Dassault Systèmes, 2025View full citation). The Uiso of the non-H atoms were grouped by chemical similarity. The Uiso of the H atoms were fixed at 1.2× the Uiso of the heavy atom to which they are attached. The peak profiles were described using a uniaxial microstrain model, with [001] as the unique axis. The background was modeled using a six-term shifted Chebyshev polynomial, with a peak at 6.00° to model the scattering from the Kapton capillary and any amorphous component of the sample.

The final refinement of 85 variables using 26,501 observations and 50 restraints yielded the residuals Rwp = 0.1055 and GOF = 2.74. The largest peak (0.24 Å from N3) and hole (0.82 Å from C6) in the difference Fourier map were calculated to be 0.56 (11) and −0.45 (11) e Å−3, respectively. The final Rietveld plot is shown in Fig. 6[link]. The largest features in the normalized error plot are in the shapes of some of the strong low-angle peaks.

[Figure 6]
Figure 6
The Rietveld plot for (I). The blue crosses represent the observed data points, and the green line is the calculated pattern. The cyan curve is the normalized error plot, and the red line is the background curve. The blue tick marks indicate the peak positions. The vertical scale has been multiplied by a factor of 10× for 2θ > 12.0°, and by a factor of 40× for 2θ > 21.8°.

The crystal structure of (I) was optimized (fixed experimental unit cell) with density functional theory techniques using VASP (Kresse & Furthmüller, 1996View full citation) through the MedeA graphical inter­face (Materials Design, 2024View full citation). The calculation was carried out on 32 cores of a 144-core (768 GB memory) HPE Superdome Flex 280 Linux server at North Central College. The calculation used the GGA-PBE functional, a plane wave cutoff energy of 400.0 eV, and a k-point spacing of 0.5 Å−1 leading to a 2 × 2 × 1 mesh, and took ∼8.5 h. Single-point density functional theory calculations (fixed experimental cell) and population analysis were carried out using CRYSTAL23 (Erba et al., 2023View full citation). The basis sets for the H, C, N and O atoms in the calculation were those of Gatti et al. (1994View full citation). The calculations were run on a 3.5 GHz PC using 8 k-points and the B3LYP functional, and took ∼1.9 h. The powder pattern of (I) has been submitted to ICDD for inclusion in the Powder Diffraction File.>

Supporting information

CCDC references: 2587069; 2587068

Crystal structure: contains datablocks I, I_VASP. DOI: https://doi.org/10.1107/S2056989026009497/hb8243sup1.cif

checkCIF report


Computing details top

3-[(1R,2S)-2-Azaniumyl-1-hydroxypropyl]phenol (2S,3S)-hydrogen 2,3-dihydroxybutanedioate (I) top
Crystal data top
C9H14NO2+·C4H5O6−Z = 4
Mr = 317.29Dx = 1.409 Mg m−3
Orthorhombic, P212121Synchrotron radiation, λ = 0.46873 Å
a = 7.190512 (12) ŵ = 0.001 mm−1
b = 8.421634 (17) ÅT = 295 K
c = 24.69323 (5) Åcylinder, 2.0 × 1.5 mm
V = 1495.32 (1) Å3
Data collection top
11-BM, APS
diffractometer		Scan method: step
Specimen mounting: Kapton capillary2θmin = 0.510°, 2θmax = 49.995°, 2θstep = 0.001°
Data collection mode: transmission
Refinement top
Least-squares matrix: full85 parameters
Rp = 0.09050 restraints
Rwp = 0.10519 constraints
Rexp = 0.039Weighting scheme based on measured s.u.'s
R(F2) = 0.09024(Δ/σ)max = 2.873
49486 data pointsBackground function: Background function: "chebyschev-1" function with 6 terms: 44.39(10), -9.67(15), -6.44(12), -0.91(18), 1.31(17), -5.45(13), Background peak parameters: pos, int, sig, gam: 5.974(12), 1.053(24)e4, 1.09(3)e4, 0.100,
Profile function: Finger-Cox-Jephcoat function parameters U, V, W, X, Y, SH/L: peak variance(Gauss) = Utan(Th)2+Vtan(Th)+W: peak HW(Lorentz) = X/cos(Th)+Ytan(Th); SH/L = S/L+H/L U, V, W in (centideg)2, X & Y in centideg 1.163, -0.126, 0.063, 0.000, 0.000, 0.002,Preferred orientation correction: Simple spherical harmonic correction Order = 2 Coefficients: 0:0:C(2,0) = -0.0120; 0:0:C(2,2) = 0.0660
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3342 (4)0.8022 (3)0.93215 (10)0.0479 (6)*
O20.3359 (4)0.5307 (3)1.10736 (10)0.0445 (5)*
N30.4468 (4)0.6614 (4)0.82720 (13)0.0479 (6)*
C40.2734 (5)0.6488 (4)0.91486 (13)0.0479 (6)*
C50.4270 (5)0.5755 (4)0.87984 (13)0.0479 (6)*
C60.2282 (5)0.5511 (4)0.96343 (12)0.0445 (5)*
C70.6176 (5)0.5688 (5)0.90906 (15)0.0479 (6)*
C80.3051 (6)0.5873 (4)1.01338 (14)0.0445 (5)*
C90.1121 (5)0.4235 (4)0.95835 (13)0.0445 (5)*
C100.2652 (5)0.4938 (4)1.05747 (11)0.0445 (5)*
C110.0749 (5)0.3274 (4)1.00251 (17)0.0445 (5)*
C120.1529 (6)0.3636 (4)1.05258 (13)0.0445 (5)*
H130.149300.667500.890800.0665*
H140.384110.456680.866200.0665*
H150.605000.495800.943400.0665*
H160.708490.498560.882440.0665*
H170.673500.674800.913300.0665*
H180.404600.687101.015800.0655*
H190.046300.387700.920000.0655*
H200.345200.747400.825800.0665*
H210.430100.593300.794300.0665*
H220.248800.874500.922300.0665*
H23−0.027300.229501.000700.0655*
H240.112200.297001.089400.0655*
H250.257700.600101.127100.0655*
O260.5203 (4)1.2468 (3)0.80511 (12)0.0480 (4)*
O270.5292 (3)0.9921 (3)0.83009 (11)0.0480 (4)*
O28−0.1329 (3)1.0797 (3)0.73408 (11)0.0480 (4)*
O300.1607 (4)0.9700 (3)0.83668 (10)0.0480 (4)*
O310.2265 (3)1.0825 (3)0.72509 (10)0.0480 (4)*
C320.2339 (5)1.1202 (4)0.82380 (14)0.0480 (4)*
C330.4494 (4)1.1141 (4)0.82050 (19)0.0480 (4)*
C340.1555 (5)1.1747 (4)0.76783 (14)0.0480 (4)*
C35−0.0592 (4)1.1695 (5)0.76762 (16)0.0480 (4)*
H360.183200.976500.726000.0675*
H370.226300.927800.868200.0675*
H380.194201.301000.765400.0675*
H390.198601.210300.852500.0675*
O29−0.1365 (4)1.2557 (3)0.80333 (12)0.0480 (4)*
H400.577130.717600.825170.0665*
H41−0.267401.253800.803700.0675*
Geometric parameters (Å, º) top
O1—C41.429 (3)H15—C71.052 (4)
O1—H220.898 (3)H16—C71.100 (4)
O2—C101.369 (3)H17—C70.984 (4)
O2—H250.946 (3)H18—C81.106 (3)
N3—C51.494 (3)H19—C91.101 (3)
N3—H201.029 (3)H20—N31.029 (3)
N3—H211.002 (3)H21—N31.002 (3)
N3—H401.051 (3)H22—O10.898 (3)
C4—O11.429 (3)H23—C111.106 (3)
C4—C51.533 (3)H24—C121.108 (3)
C4—C61.491 (3)H25—O20.946 (3)
C4—H131.083 (3)O26—C331.286 (3)
C5—N31.494 (3)O27—C331.200 (3)
C5—C41.533 (3)O28—C351.241 (3)
C5—C71.550 (4)O30—C321.407 (3)
C5—H141.100 (3)O30—H370.977 (3)
C6—C41.491 (3)O31—C341.406 (3)
C6—C81.386 (3)O31—H360.946 (3)
C6—C91.366 (3)C32—O301.407 (3)
C7—C51.550 (4)C32—C331.553 (3)
C7—H151.052 (4)C32—C341.562 (4)
C7—H161.100 (4)C32—H391.069 (3)
C7—H170.984 (4)C33—O261.286 (3)
C8—C61.386 (3)C33—O271.200 (3)
C8—C101.374 (3)C33—C321.553 (3)
C8—H181.106 (3)C34—O311.406 (3)
C9—C61.366 (3)C34—C321.562 (4)
C9—C111.384 (3)C34—C351.544 (3)
C9—H191.101 (3)C34—H381.101 (4)
C10—O21.369 (3)C35—O281.241 (3)
C10—C81.374 (3)C35—C341.544 (3)
C10—C121.367 (3)C35—O291.270 (3)
C11—C91.384 (3)H36—O310.946 (3)
C11—C121.391 (3)H37—O300.977 (3)
C11—H231.106 (3)H38—C341.101 (4)
C12—C101.367 (3)H39—C321.069 (3)
C12—C111.391 (3)O29—C351.270 (3)
C12—H241.108 (3)O29—H410.942 (3)
H13—C41.083 (3)H40—N31.051 (3)
H14—C51.100 (3)H41—O290.942 (3)
C4—O1—H22108.8 (3)C6—C9—H19123.8 (3)
C10—O2—H25112.5 (3)C11—C9—H19115.8 (3)
C5—N3—H20107.6 (3)O2—C10—C8120.4 (3)
C5—N3—H21114.6 (3)O2—C10—C12118.8 (3)
H20—N3—H21106.9 (3)C8—C10—C12120.85 (19)
C5—N3—H40110.1 (3)C9—C11—C12119.6 (2)
H20—N3—H40108.3 (3)C9—C11—H23122.2 (4)
H21—N3—H40109.0 (3)C12—C11—H23117.8 (4)
O1—C4—C5108.2 (3)C10—C12—C11119.5 (2)
O1—C4—C6109.0 (3)C10—C12—H24119.3 (3)
C5—C4—C6112.9 (3)C11—C12—H24120.8 (4)
O1—C4—H13106.5 (3)C32—O30—H37109.1 (3)
C5—C4—H13110.1 (3)C34—O31—H36112.6 (3)
C6—C4—H13110.0 (3)O30—C32—C33110.8 (3)
N3—C5—C4111.4 (3)O30—C32—C34109.3 (3)
N3—C5—C7109.8 (3)C33—C32—C34108.9 (3)
C4—C5—C7112.9 (3)O30—C32—H39113.6 (3)
N3—C5—H14101.6 (3)C33—C32—H39107.2 (3)
C4—C5—H14109.7 (3)C34—C32—H39107.0 (3)
C7—C5—H14111.0 (3)O26—C33—O27127.8 (3)
C4—C6—C8120.5 (3)O26—C33—C32112.5 (3)
C4—C6—C9119.6 (3)O27—C33—C32119.7 (3)
C8—C6—C9119.89 (19)O31—C34—C32111.8 (3)
C5—C7—H15108.7 (3)O31—C34—C35110.2 (3)
C5—C7—H16105.5 (3)C32—C34—C35110.8 (3)
H15—C7—H16102.6 (3)O31—C34—H38113.6 (3)
C5—C7—H17112.2 (4)C32—C34—H38103.9 (3)
H15—C7—H17118.7 (4)C35—C34—H38106.3 (3)
H16—C7—H17108.0 (3)O28—C35—C34116.5 (3)
C6—C8—C10119.74 (17)O28—C35—O29128.7 (3)
C6—C8—H18118.3 (3)C34—C35—O29114.8 (3)
C10—C8—H18121.9 (3)C35—O29—H41115.8 (3)
C6—C9—C11120.4 (2)
(I_VASP) top
Crystal data top
C9H14NO2+·C4H5O6−b = 8.42062 Å
Mr = 317.29c = 24.69000 Å
Orthorhombic, P212121V = 1494.81 Å3
a = 7.18988 ÅZ = 4
Data collection top
h = →l = →
k = →
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzBiso*/Beq
O10.199040.796410.90895
O20.303670.553121.09380
N30.439930.674410.82696
C40.207280.626340.89994
C50.400940.582340.87743
C60.164770.536590.95149
C70.565410.598390.91583
C80.245060.586581.00022
C90.047890.403820.95093
C100.213640.502471.04809
C110.013400.322100.99913
C120.095850.369591.04753
H130.104430.594110.86857
H140.390330.457830.86419
H150.554820.513290.94926
H160.695320.573320.89398
H170.575430.718240.93284
H180.331910.692781.00118
H19−0.017070.365380.91312
H200.450570.797660.83301
H210.336070.652490.79796
H220.069610.823810.91785
H23−0.079790.220030.99895
H240.071840.302911.08469
H250.231330.519701.12653
H400.568030.639050.81033
O260.523211.255110.80787
O270.537120.995710.83047
O28−0.146931.091190.73653
O300.163460.956610.81546
O310.213011.108370.71535
C320.234281.112680.81422
C330.448861.118910.81698
C340.153051.189260.76289
C35−0.059251.182890.76641
H360.154461.002320.71438
H370.186950.907280.85137
H380.197931.313620.75953
H390.184811.183680.84927
O29−0.135481.276460.80279
H41−0.2918701258050.80531
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O29—H41···O26i1.141.332.464173
O30—H37···O10.991.702.686169
O31—H36···O29ii0.991.952.885156
O31—H36···O280.992.362.64496
N3—H40···O31iii1.051.722.762172
N3—H21···O28ii1.051.692.718166
N3—H20···O271.051.782.796161
N3—H20···O301.052.503.111116
O2—H25···O27iv1.001.762.709157
O1—H22···O2iv0.982.193.113155
C5—H14···O261.102.403.364145
C12—H24···O261.092.723.758154
C4—H13···O281.112.613.410128
C9—H19···O291.092.954.033171
Symmetry codes: (i) x−1, y, z; (ii) −x, y−1/2, −z+3/2; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, −y+3/2, −z+2.
 

Acknowledgements

Use of the Advanced Photon Source at Argonne National Laboratory was supported by the U. S. Department of Energy, Office of Science, Office of Basic Energy Sciences, under Contract No. DE-AC02–06CH11357. We thank Saul Lapidus for his assistance in the data collection. We also thank the ICDD team – Megan Rost, Steve Trimble, and Dave Bohnenberger – for their contribution to research, sample preparation, and in-house XRD data collection and verification.

Funding information

Funding for this research was provided by: International Centre for Diffraction Data (grant No. 09-03).

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Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026009497